Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.

doi:10.1021/JM00178A004

Paper

Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.

Published Apr 1, 1980 · J. Wikel, C. Paget, D. Delong

Journal of medicinal chemistry

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88

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Abstract

The synthesis and antirhinovirus activity of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine (4 and 5) are reported. The structural assignments of 4 and 5 are based upon 13C NMR spectra of both isomers and also X-ray analysis of 5. The anti-isomer 5 was more potent than the syn-isomer 4 when compared as an inhibitor of rhinovirus multiplication in vitro. Both isomers inhibited multiplication of 15 different serotypes of rhinovirus.

In Vitro Study

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Study Snapshot

Both syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine (4 and 5) effectively inhibit rhinovirus multiplication, with the anti-isome

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.

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References

Citations

An efficient trans complementation system for in vivo replication of defective poliovirus mutants

Exogenous viral proteins can efficiently rescue the replication of defective poliovirus mutants, highlighting their potential role in viral replication and protein/protein interactions during picornavirus infection.

Characterization of Anti-Poliovirus Compounds Isolated from Edible Plants

Edible plant extracts, specifically chrysophanol and vanicoside B, show potential as potent antivirals for poliovirus infection.

Enteroviral Replication Inhibition by N-Alkyl Triazolopyrimidinone Derivatives through a Non-capsid Binding Mode.

N-alkyl triazolopyrimidinone derivatives show improved antiviral activity against human rhinovirus and other enteroviruses, with compound 2c showing broad anti-hRV activity and safe CYP inhibition.

Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes.

This study presents a stereospecific 1,4-metallate rearrangement for selective and exclusive synthesis of unsymmetric diaryl oximes and Z-isomer of aryl alkyl ketoxime, enabling efficient access to isoquinolines, isoquinoline N-oxides, and amides

Poliovirus Evolution toward Independence from the Phosphatidylinositol-4 Kinase III β/Oxysterol-Binding Protein Family I Pathway.

The PI4KB/OSBP pathway is not essential for enterovirus replication in vitro, suggesting a potential evolutionary pathway towards independence from this pathway.